The Fannie Mae/Freddie Mac conforming loan limit in SD is $546,250. That can theoretically affect the math somewhat.
The fact is there is plenty of competition in the ~400k range for SFH in SD County. We found that once we started looking at homes above $450k, the options got way better than those 400-450k.
Re-reading your past post, while I admire your forward thinking, odds are your potential future wife will hate whatever house you buy now. Especially if you sink $50k into upgrades; one person’s dream kitchen can be a nightmare for someone else.
If you are handy enough to do the work yourself that’s one thing, but I’m not sure you really need or should look to buy a fixer upper at your stage in life. And frankly you’re too young and relatively affluent to live in La Mesa or Allied Gardens right now. There are nice parts of La Mesa, but it’s not exactly a place full of hip young people.
I get that you’re afraid of being priced out forever, but there’s something to be said for you renting for $1,000 a month and putting the additional $1,000 a month you’d be paying towards a mortgage into an investment account. One of the huge advantages you have as an unmarried 26 year old professional is if you get a great job offer in Seattle or San Francisco or Austin you can pick up and move tomorrow. Yes, you can rent out or sell a home if you buy one, but there is an opportunity cost there.
If they were cheaper right now I’d tell you to buy a condo in a “cool” area. Somewhere like PB or Hillcrest or North Park where you could easily rent the place down the road if you outgrow it. Buying a SFH in La Mesa for a primary residence as a young single guy feels like putting the cart before the horse to me.